D. Chiarino, M. Napoletano, A. Sala
1987
Citations
0
Influential Citations
28
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
Bromonitrile oxide 2, generated from easily available dibromoformaldoxime 1, reacts with monosubstituted acetylenic derivatives 4 to give 3-bromo-5-substituted isoxazoles 5 in high yield. The experimental conditions necessary to overcome difficulties such as the low reactivity of acetylenic dipolarophiles and the high tendency to dimerization of bromonitrile oxide 2, are discussed; the regioselectivity of this 1,3-dipolar cycloaddition is also studied. The obtained improvements in the synthesis of some pharmacologically active compounds are reported.